Terrain that has previously experienced a landslide is subject to the additional threat of reactivated landslides. The reactivated Wuwanchai landslide is located in Chiayi County in southern Taiwan at Expressway No. 18. The reactivated landslide has exhibited slow movement with continuing creek headwater erosion. The landslide comprises eight sliding blocks that are categorized as main slipping blocks, slow-moving blocks, and activated blocks in accordance with their deformation characteristics. The reactivated landslide’s deformation characteristics and failure mechanisms were monitored using field investigations, airborne LiDAR surveys, and unmanned aerial vehicle (UAV) photogrammetry; the results were compared with traditional inclinometer monitoring of the displacement and groundwater level measurements. The concave terrain tends to collect surface water, and the level of the groundwater table tends to fluctuate due to seasonal precipitation. Geologic structures and headward creek erosion increased the sliding of the deposited colluvium. An interaction mechanism for the sliding blocks is proposed on the basis of the deformation characteristics, activity of the sliding blocks, topography changes, sliding masses, and UAV images. Separation of the landslide area in accordance with the deformation characteristics of the composed sliding blocks best explained the reactivation mechanism of the large-scale landslide.